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Search results; Over 1,000 homes in Key West

Guest favourite
Flat in Key West
Downtown Apartment in Key West
1 bedroom, 2 beds, 1 private bathroom
8–13 Sept
,
4.85 out of 5 average rating, 98 reviews
Guest favourite
Houseboat in Key West
Tiki Suites ~ Original Tiki ~ Floating Bungalows
1 bedroom, 1 bed
23–28 Aug
4.91 out of 5 average rating, 558 reviews
Superhost
Home in Marathon
Waterfront Pool Home w/ Private Dock, Tiki Hut & B
4 bedrooms, 7 beds
28 Nov – 5 Dec
Featured hotel
Room in Key West
High floor island view two queen beds
2 queen beds
17–22 Aug
New place to stay
Room in Key West
*Near Smathers Beach | Pool + Dining & Bar
2 queen beds
22–27 Aug
4.8 out of 5 average rating, 20 reviews
Guest favourite
Home in Big Pine Key
Fishermen's Paradise | Pool, 220' Dock & Open-Wate
3 bedrooms, 3 beds
5–10 Oct
4.91 out of 5 average rating, 102 reviews
Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
26 Sept – 1 Oct
4.83 out of 5 average rating, 111 reviews
Guest favourite
Flat in Key West
Designer Waterfront Estate - Lunara Bay Collection
4 bedrooms, 5 beds
22–27 Aug
4.83 out of 5 average rating, 30 reviews
Top guest favourite
Home in Marathon
Waterfront 6BR Luxury Retreat w/ Pool & Dock
6 bedrooms, 10 beds
3–10 Oct
5.0 out of 5 average rating, 31 reviews
Luxe
Home in Key West
The Rigby House - Pool, One block from Duval St
6 bedrooms, 6 beds
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
20–25 Aug
4.56 out of 5 average rating, 25 reviews
Guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds
24–29 Sept
4.96 out of 5 average rating, 207 reviews
Luxe
Home in Key West
Floralee House at Lunara Bay
6 bedrooms, 9 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 39 reviews
Room in Key West
*Near Mallory Square | Resort Pool, Dining + Bar
1 king bed
17–22 Aug
4.8 out of 5 average rating, 10 reviews
Guest favourite
Home in Marathon
Lagoona-Matata
3 bedrooms, 4 beds
28 Aug – 4 Sept
5.0 out of 5 average rating, 5 reviews
Home in Marathon
Luxurious 3BR Gulffront | Pool | Dock | Patio
3 bedrooms, 4 beds
23–30 Aug
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Marathon
*NEW* Reel Escape~Dock!~Lift!~Pet Friendly~Grill!
3 bedrooms, 3 beds
22–29 Aug
New place to stay
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds
8–15 Sept
4.86 out of 5 average rating, 36 reviews